People in other big-city school districts around the country have a hard
time thinking of Portland Public Schools as a truly urban district.

Not only is Portland tiny (47,000 students, compared with 700,000 in Los
Angeles), but only 43 percent of its students are poor (in Chicago, 85
percent are). A majority are white (in Philadelphia, 13 percent are).
What's more, middle- and upper-income professionals in Portland do
something their counterparts in Detroit, L.A. or Washington, D.C.,
rarely consider: They send their children to central-city public
schools.

But there is one way in which our small, mostly white, heavily
middle-class school system is statistically right in line with some of
the grittiest urban districts in the nation: A shockingly low share of
Portland's high school students earn diplomas.

As The Oregonian reported on the front page recently, just 53 percent of
Portland's high school students graduate in four years.

That puts our dropout rate on par with rates in Philadelphia, Louisville
and El Paso -- all bigger districts with much higher concentrations of
poverty.

Contrast that with New York City. That heavily impoverished district,
with more than 1 million students and a historically intransigent
teachers union, has boosted its four-year graduation rate to 63 percent,
up from 47 percent in 2005. That's right -- New York City's high school
graduation rate is 10 percentage points higher than Portland's.

It's not that Portland hasn't tried to do better. The school district
has implemented a series of reforms, many of them strikingly similar to
what New York City has done. A few of them -- turning to private outfits
to run schools, upending the faculty and teaching methods at schools
with chronic low test scores, using sophisticated data systems to
pinpoint instructional needs -- are steps the Obama administration wants
to encourage all school districts with achievement problems to adopt.

But in Portland, those reforms haven't worked. Despite 15 years of
effort, the city's graduation rate hasn't budged.

How Portland took good ideas and managed to botch their implementation
-- through inattention and a failure to measure and demand results -- is
a cautionary tale for those in Washington who want to use federal
dollars to get local schools to do right by their students.

How Portland residents have quietly tolerated the lifelong harm done to
thousands of its young people each year is harder to explain. Young
adults without high school diplomas will forever find doors shut in
their faces and will lose out on a half-million dollars, on average, in
potential lifetime earnings. Has our city's famous laid-back tolerance
of different life paths lulled us into acceptance as nearly half of our
high school students go over an educational cliff?

Portland's first effort to grapple with its dropout problem began in the
mid-1990s, when the school district vastly expanded what was then a
small network of community-based alternative high schools. Founded in
the 1970s and '80s, these privately run nonprofit programs had a good
reputation for welcoming troubled teens who had dropped out of
traditional high schools and reconnecting them to the classroom and
society.

Expanding these schools seemed like a good way to benefit more
vulnerable young people. It also happened to benefit the school
district's bottom line. Voter-enacted changes in the way Oregon funds
schools hit Portland Public Schools hard in the early 1990s. The surest
and quickest way to refill district coffers was to lure back students
who had dropped out.

It seemed like a win-win: Disconnected students could find their niche
in a nontraditional school setting, and the Portland school system could
keep up to 20 percent of the state funds that paid for them to be
there. Enrollment in the alternative programs doubled between 1991 and
1997.

National meetings were convened in Portland to let other youth-helping
agencies see firsthand the variety and power of Portland's second-chance
alternative schools. New York, Philadelphia and others created similar
networks of community-based schools with nontraditional structures and
extra social and emotional support to help dropouts or near dropouts get
back on track.

The city's second stab at fixing its dropout problem began in the early
2000s. The Bill & Melinda Gates Foundation was pouring major money
into promoting a particular school reform idea: breaking up big,
institutional high schools to create small, personalized ones.
Researchers had found links between these more intimate school settings
and higher test scores and graduation rates.

Leading Portland-area employers teamed with Oregon's biggest
philanthropy, the Meyer Memorial Trust, and Gates to pour $2.1 million
into remaking three of the city's big traditional high schools -- those
with the most disadvantaged students and the worst dropout rates. The
schools were broken up into multiple small academies housed under one
roof, each with its own defined academic theme, such as
business-technology and renaissance arts.

As those campuses were reorganizing, another effort got under way: an
unprecedented study, also funded by Gates and other foundations, of who
drops out in Portland and why.

Released in May 2007, the study tracked every student in the class of
2004 and yielded three major findings. First, the dropout problem was
much bigger than the state or school district had let on: The on-time
graduation rate was not 85 percent, as had long been officially
reported, but 54 percent.

Second, it isn't just poor and minority students who drop out; white
kids do, too, at alarming rates. In fact, a majority of Portland's
dropouts are white, only half qualify for subsidized school meals, and
90 percent are native English speakers.

Finally, and of most interest to school district leaders, likely
dropouts could be pinpointed as early as ninth grade based on
attendance, test scores and grades. Students of any race or family
background who failed to accumulate 5.5 credits in ninth grade were four
times more likely to drop out than those who earned enough credits.

The study sparked immediate action. Then-Superintendent Vicki Phillips,
now head of education initiatives at Gates, created an "academic
priority" program in which the district identified by name all incoming
ninth-graders with the most risk factors for failing to earn 5.5
credits.

High schools were given an average of $120,000 apiece to design their
own approaches to helping these students. Some schools used the money to
reduce class sizes in ninth grade and asked their best teachers to
teach them. Others assigned blocks of freshmen to a common set of core
academic teachers who met together to monitor their progress. Still
others appointed adult mentors to conduct daily or weekly check-ins with
the shakiest students.

In theory, the strategies Portland chose -- plentiful and welcoming
alternative schools, innovative small academies in place of traditional
big high schools and targeted extra support for ninth-graders at risk of
failure -- were smart ones. They have certainly worked elsewhere.

New York City's small high schools showed slightly higher graduation
rates just a couple of years after they opened. Philadelphia's growing
network of alternative high schools has brought positive results.
Researchers in Chicago and Baltimore confirmed that identifying at-risk
students by eighth and ninth grade, and helping them pass enough classes
to be on track toward graduation, is the best way to prevent dropouts.

But in Portland, these same steps haven't led to any measurable
improvement in the high school graduation rate. The reason is that in
each case, the school district failed to press for results and to fight
against -- or even to recognize -- the political, cultural and
bureaucratic forces that typically undermine reform.

Take the "academic priority" program for at-risk ninth-graders. Leaving
it up to individual schools to design their own interventions probably
made sense -- the district's central office certainly had no monopoly on
good ideas.

But for such a decentralized strategy to work, the district needed to
measure and reward outcomes so that the principals and teachers would
have an incentive to drop practices that weren't working and adopt
others that were. The district failed to do so. Three years into the
project, there has yet to be a public report on how many "priority"
freshmen at each school passed their classes or earned enough high
school credits after getting extra attention.

A few of the high schools did remarkably better than others at keeping
at-risk students on track, yet their practices have yet to be showcased,
let alone pressed upon other far-less-successful schools -- part of the
district's long-standing culture of letting schools choose their own
paths and hesitating to call out any schools' success for fear of
hurting feelings at those that aren't as good.

The city's effort to break up its big high schools into smaller
schools-within-schools suffered a similar fate.

When Portland won grants to create the small schools, backers pledged
that students would be known, nurtured and challenged so well that 97
percent would earn diplomas. But, five years into the Gates-led
initiative, overall graduation rates at Roosevelt and Marshall high
schools' small academies remain stuck at the same unacceptably low level
of the old comprehensive high schools they replaced. The Madison High
faculty revolted and reverted to the big school model.

Why the inability to improve? A big reason was the federal No Child Left
Behind law, which required giving students at failing schools the
ability to transfer out. Most students who could read and write at grade
level opted to flee, leaving higher concentrations of lower-achieving
students at the smaller schools.

But the schools never had much of a chance to compete because they never
had real autonomy. New York City hired full-fledged principals for its
new small high schools and gave them the ability to hire their own
teachers. Portland paid small-school principals what it paid vice
principals at large schools and vetted their qualifications at that
same, lesser standard. Teachers who were on staff at the big schools
were shunted into and among the small-school faculties, whether or not
they or the small schools considered that the right fit.

Portland's biggest failure has been its community-based alternative
schools. In 2007, the most recent year on which the district has
reported, these privately run schools enrolled about 2,500 students but
issued just 156 diplomas. By contrast, New York City's alternative
schools now issue diplomas to more than half the overage, undercredited
students who enter them.

The reason for this staggering difference has to do with expectations
and accountability. In 2004, New York schools Chancellor Joel Klein
closed a host of dropout recovery programs that weren't getting the job
done. The district now issues detailed yearly performance reports on
each of its transfer high schools, and schools that don't measure up
risk being shut down.

"One of the principles that drive the New York effort is the belief that
all kids can graduate," says JoEllen Lynch, former executive director
of the Office of Multiple Pathways to Graduation in New York. "Those
students need a lot more support, instructionally and emotionally, but
you have to move them toward a diploma. That's just a basic expectation
of a school."

Such expectations and accountability have never been part of Portland's
alternative schools system. The way school district and city leaders see
it, getting disengaged teens to reconnect with school is a victory in
itself. The alternative schools are funded with public money, but
because they are privately operated, they are not subject to state
accountability reports on their test scores or graduation rates.

The youth-embracing vibe inside the schools reflects the low
expectations. Earning credits, mastering algebra and learning to use
proper spelling and grammar can seem downright square. Preparing for the
GED -- a vastly substandard credential to a diploma -- is considered
rigorous. In some of the programs, students can take classes on comfy
couches, bring their guitars to class and spend hours talking about
current events -- all engaging, but not the ticket to a proper high
school diploma, much less college or career.

The high-sympathy, low-demand ethos has made the alternative schools
wildly popular with young adults turned off by the city's traditional
high schools (not to mention magnets for troubled and listless teens
from nearby school districts). In New York City, about 5 percent of high
school students attend community-based second-chance alternative high
schools, known there as "transfer high schools"; in Portland, nearly 20
percent do.

Having such a large portion of the city's students in alternative
schools can depress a district's graduation rate by excusing regular
middle and high schools from addressing students' problems early on,
notes Robert Balfanz, a Johns Hopkins University researcher who
specializes in dropouts. "School officials can say, 'Well, we have lots
of good alternative schools for students who need more support than we
can give, so the best solution is really to try to get these students
there,'" rather than provide supports or prevention services in our
regular schools, he said.

None of this should be news in Portland, by the way. The Oregonian has
run several front-page articles showing that the alternative schools
have poor attendance, weak oversight, lax academic expectations and
extremely few graduates.

The potentially good news is that the Portland schools are beginning to
show signs of waking up. Superintendent Carole Smith, who spent decades
running one of the city's better private alternative schools, has
indicated that the district will start vetting such schools more
stringently for 2011, cutting off contracts to those that don't measure
up. She has also said that this fall the district will begin posting
data on at-risk freshmen at the traditional high schools who are
supposed to be getting extra support and attention under the "academic
priority" program. That should make it possible for the public to see
how good a job individual schools are doing in helping at-risk freshmen
pass their classes and earn sufficient credits to graduate.

In the face of declining enrollment, Smith is also pressing her plan to
close one or more high schools and lessen the socioeconomic gulfs
between those that remain. Her hope is that having fewer, larger
neighborhood high schools -- the opposite of the Gates approach -- will
allow each one to guarantee more catch-up opportunities for struggling
students, plus an array of fine arts, music, college prep and world
languages now lacking in some high-poverty Portland high schools.

Smith's focus on improving the district's graduation rate -- she calls
it "our primary challenge" -- is welcome. But delivering results will
require a serious change in expectations at school district headquarters
and around the city.

The attitude that has long infused Portland's alternative schools --
that troubled teens can't be expected to graduate and that just getting
them to show up is a victory -- has also defined Portland's general
approach to the dropout problem. Grant makers and school board members
praised the district for its creativity and partnerships in addressing
the dropout issue, even as the schools kept failing huge numbers of
students. Good intentions were rewarded, not results. If New York and
Philadelphia can improve their graduation rates, what excuse does
Portland have not to do so, too?

Betsy Hammond covers Portland schools for The Oregonian. This article
originally ran in the Washington Monthly as part of a larger special
section called Fighting the Dropout Crisis and is reprinted with
permission. Read the full report from the July/August issue of the
magazine at washingtonmonthly.com